Probing the relevance of lectin clustering for the reliable evaluation of multivalent carbohydrate recognition

Journal of the American Chemical Society

Volumn 131, Issue 49, 2009, Pages 17765-17767

  Munoz, Eva Maria ^a   Correa, Juan ^a   Fernandez Megia, Eduardo ^a   Riguera, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING EFFICIENCY; CARBOHYDRATE RECOGNITION; SURFACE-BASED;

CARBOHYDRATES;

SURFACE PLASMON RESONANCE;

CARBOHYDRATE; LECTIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; CLUSTER ANALYSIS; PROTEIN BINDING; PROTEIN INTERACTION;

CONCANAVALIN A; DENDRIMERS; GALLIC ACID; MANNOSE; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS; SURFACE PROPERTIES;

EID: 71749092320     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9074826     Document Type: Article

References (48)

1. (a) Sharon, N. Biochim. Biophys. Acta 2006, 1760, 527.
2. (b) Haltiwanger, R. S.; Lowe, J. B. Annu. Rev. Biochem. 2004, 73, 491.
3. (c) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
4. (d) Lis, H.; Sharon, N. Chem. Rev. 1998, 98, 637.
5. (a) Kiessling, L. L.; Young, T.; Gruber, T. D.; Mortell, K. H. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B. O., Tatsuta, K., Thiem, J., Eds.; Springer: 2008; p 2483.
6. (b) Dam, T. K.; Brewer, C. F. Biochemistry 2008, 47, 8470.
7. (c) Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555.
8. (d) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754.
9. (e) Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692.
10. (a) Pieters, R. J. Org. Biomol. Chem. 2009, 7, 2013.
11. (b) Pieters, R. J. Med. Res. Rev. 2007, 27, 796.
12. (c) Spain, S. G.; Gibson, M. I.; Cameron, N. R. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2059.
13. (a) Imberty, A.; Chabre, Y. M.; Roy, R. Chem.-Eur. J. 2008, 14, 7490.
14. (b) Chabre, Y. M.; Roy, R. Curr. Top. Med. Chem. 2008, 8, 1237.
15. (a) Duverger, E.; Frison, N.; Roche, A.-C.; Monsigny, M. Biochimie 2003, 85, 167.
16. (b) Haseley, S. R.; Kamerling, J. P.; Vliegenthart, J. F. G. Top. Curr. Chem. 2002, 218, 93.
17. (c) Dam, T. K.; Brewer, C. F. Chem. Rev. 2002, 102, 387.
18. (a) Tabarani, G.; Reina, J. J.; Ebel, C.; Vivès, C.; Lortat-Jacob, H.; Rojo, J.; Fieschi, F. FEBS Lett. 2006, 580, 2402.
19. (b) Nieba, L.; Krebber, A.; Plückthun, A. Anal. Biochem. 1996, 234, 155.
20. (a) Piliarik, M.; Vaisocherová, H.; Homola, J. In Biosensors and Biodetection; Rasooly, A., Herold, K. E., Eds.; Humana Press: 2009; p 65.
21. (b) Rich, R. L.; Myszka, D. G. J. Mol. Recognit. 2008, 21, 355.
22. (c) Homola, J. Chem. Rev. 2008, 108, 462.
23. Although a few SPR studies have previously evaluated the binding efficacy of multivalent glycoconjugates towards immobilized lectins, these reports usually underestimate the real complexity of the interaction by either analyzing data using simple binding models (that do not describe well the complex binding mechanism) or considering avidity as an undesired event interfering with data analysis: (a) Murthy, B. N.; Sinha, S.; Surolia, A.; Indi, S. S.; Jayaraman, N. Glycoconjugate J. 2008, 25, 313.
24. (b) Srinivas, O.; Larrieu, P.; Duverger, E.; Bousser, M.-T.; Monsigny, M.; Fonteneau, J.-F.; Jotereau, F.; Roche, A.-C. Bioconjugate Chem. 2007, 18, 1547.
25. (c) Hasegawa, T.; Numata, M.; Okumura, S.; Kimura, T.; Sakurai, K.; Shinkai, S. Org. Biomol. Chem. 2007, 5, 2404.
26. (d) Murthy, B. N.; Voelcker, N. H.; Jayaraman, N. Glycobiology 2006, 16, 822.
27. (e) Terada, T.; Nishikawa, M.; Yamashita, F.; Hashida, M. J. Pharm. Biomed. Anal. 2006, 41, 966.
28. (f) Mislovicová, D.; Masárová, J.; Svitel, J.; Mendichi, R.; Soltés, L.; Gemeiner, P.; Danielsson, B. Bioconjugate Chem. 2002, 13, 136.
29. (g) Thomas, C. J.; Surolia, A. Arch. Biochem. Biophys. 2000, 374, 8.
30. For an interesting example of adjusting the equilibrium to more complex models, see: (a) Jule, E.; Nagasaki, Y.; Kataoka, K. Bioconjugate Chem. 2003, 14, 177.
31. (b) Jule, E.; Nagasaki, Y.; Kataoka, K. Langmuir 2002, 18, 10334. See also ref 6a.
32. (a) Fernandez-Megia, E.; Correa, J.; Rodriguez-Meizoso, I.; Riguera, R. Macromolecules 2006, 39, 2113.
33. (b) Fernandez-Megia, E.; Correa, J.; Riguera, R. Biomacromolecules 2006, 7, 3104.
34. D of each glycodendrimer-Con A complex. Yung-Chi, C.; Prusoff, W. H. Biochem. Pharmacol. 1973, 22, 3099.
35. (a) Woller, E. K.; Walter, E. D.; Morgan, J. R.; Singel, D. J.; Cloninger, M. J. J. Am. Chem. Soc. 2003, 125, 8820.
36. (b) Pohl, N. L.; Kiessling, L. L. Synthesis 1999, 1999, 1515.
37. Mann, D. A.; Kanai, M.; Maly, D. J.; Kiessling, L. L. J. Am. Chem. Soc. 1998, 120, 10575.
38. h of glycosylated GATG dendrimers (G1-G3) is 0.7-1.6 nm.
39. (a) Liang, P.-H.; Wang, S.-K.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11177.
40. (b) Mandal, D. K.; Kishore, N.; Brewer, C. F. Biochemistry 1994, 33, 1149.
41. -1 was considered.
42. D,low for Con A-HD is best described by a range of values, while, for Con A-LD, the binding isotherm fitted better with a 1:1 Langmuir model.
43. mono)αN] proposed by Whitesides (ref 2d), an αN = 2.14 results, indicative of a bivalent binding mode. See also: Wolfenden, M. L.; Cloninger, M. J. J. Am. Chem. Soc. 2005, 127, 12168.
44. (a) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed. 2006, 45, 2348.
45. (b) Cambi, A.; de Lange, F.; van Maarseveen, N. M.; Nijhuis, M.; Joosten, B.; van Dijk, E. M. H. P.; de Bakker, B. I.; Fransen, J. A. M.; Bovee-Geurts, P. H. M.; van Leeuwen, F. N.; Van Hulst, N. F.; Figdor, C. G. J. Cell Biol. 2004, 164, 145.
46. (c) Brewer, C. F.; Miceli, M. C.; Baum, L. G. Curr. Opin. Struct. Biol. 2002, 12, 616.
47. (c) Hakomori, S.-i. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 225.
48. Gopalakrishnan, M.; Forsten-Williams, K.; Cassino, T.; Padro, L.; Ryan, T.; Täuber, U. Eur. Biophys. J. 2005, 34, 943.